Hastatoside

Details

• Internal ID: cabb7f55-f9f5-49d1-aa82-889ccd822514
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: methyl (1S,4aR,7S,7aR)-4a-hydroxy-7-methyl-5-oxo-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,6,7,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
• InChI: InChI=1S/C17H24O11/c1-6-3-9(19)17(24)7(14(23)25-2)5-26-15(10(6)17)28-16-13(22)12(21)11(20)8(4-18)27-16/h5-6,8,10-13,15-16,18,20-22,24H,3-4H2,1-2H3/t6-,8+,10-,11+,12-,13+,15-,16-,17+/m0/s1
• InChI Key: PRZVXHGUJJPSME-CZMSZWGTSA-N
• Popularity: 13 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₄O₁₁
• Molecular Weight: 404.40 g/mol
• Exact Mass: 404.13186158 g/mol
• Topological Polar Surface Area (TPSA): 172.00 Ų
• XlogP: -1.70
• Atomic LogP (AlogP): -2.83
• H-Bond Acceptor: 11
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

• 50816-24-5
• 5-Hydroxyverbenalin
• Y7WKJ7982U
• 1alpha-(beta-D-Glucopyranosyloxy)-1,4a,5,6,7,7aalpha-hexahydro-4aalpha-hydroxy-7alpha-methyl-5-oxocyclopenta[c]pyran-4-carboxylic acid methyl ester
• methyl (1S,4aR,7S,7aR)-4a-hydroxy-7-methyl-5-oxo-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,6,7,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
• CHEBI:178050
• DTXSID30904209
• methyl (1S,4aR,7S,7aR)-1-(beta-D-glucopyranosyloxy)-4a-hydroxy-7-methyl-5-oxo-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
• Methyl (1S,4aR,7S,7aR)-4a-hydroxy-7-methyl-5-oxo-1-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy)-1H,4ah,5H,6H,7H,7ah-cyclopenta(C)pyran-4-carboxylate
• 1.ALPHA.-(.BETA.-D-GLUCOPYRANOSYLOXY)-1,4A,5,6,7,7A.ALPHA.-HEXAHYDRO-4A.ALPHA.-HYDROXY-7.ALPHA.-METHYL-5-OXOCYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID METHYL ESTER
• 1alpha-(beta-D-Glucopyranosyloxy)-1,4a,5,6,7,7aalpha-hexahydro-4aalpha-hydroxy-7alpha-methyl-5-oxocyclopenta(C)pyran-4-carboxylic acid methyl ester
• CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 1-(.BETA.-D-GLUCOPYRANOSYLOXY)-1,4A,5,6,7,7A-HEXAHYDRO-4A-HYDROXY-7-METHYL-5-OXO-, METHYL ESTER, (1S,4AR,7S,7AR)-
• CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 1-(.BETA.-D-GLUCOPYRANOSYLOXY)-1,4A,5,6,7,7A-HEXAHYDRO-4A-HYDROXY-7-METHYL-5-OXO-, METHYL ESTER, (1S-(1.ALPHA.,4A.ALPHA.,7.ALPHA.,7A.ALPHA.))-
• Cyclopenta(C)pyran-4-carboxylic acid, 1-(beta-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-4a-hydroxy-7-methyl-5-oxo-, methyl ester, (1S,4aR,7S,7aR)-
• Cyclopenta(C)pyran-4-carboxylic acid, 1-(beta-D-glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-4a-hydroxy-7-methyl-5-oxo-, methyl ester, (1S-(1alpha,4aalpha,7alpha,7aalpha))-
• methyl (1S,4aR,7S,7aR)-4a-hydroxy-7-methyl-5-oxo-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-carboxylate
• methyl (1S,4aR,7S,7aR)-1-(beta-D-glucopyranosyloxy)-4a-hydroxy-7-methyl-5-oxo-1,4a,5,6,7,7a-hexahydrocyclopenta(c)pyran-4-carboxylate
• methyl (1S,4aR,7S,7aR)-4a-hydroxy-7-methyl-5-oxo-1-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy-1,6,7,7a-tetrahydrocyclopenta(c)pyran-4-carboxylate
• RefChem:145320
• DTXCID901333358
• PRZVXHGUJJPSME-UHFFFAOYSA-N
• MFCD09752811
• Hastatoside (Standard)
• UNII-Y7WKJ7982U
• orb1301520
• SCHEMBL30819230
• HY-N2015R
• WLZ4691
• 1|A-(|A-D-Glucopyranosyloxy)-1,4a,5,6,7,7a|A-hexahydro-4a|A-hydroxy-7|A-methyl-5-oxocyclopenta[c]pyran-4-carboxylic acid methyl ester
• HY-N2015
• MSK157223
• s9026
• AKOS040758802
• CCG-268688
• EBC-617749
• AC-34591
• DA-53849
• Methyl (1S,4aR,7S,7aR)-4a-hydroxy-7-methyl-5-oxo-1-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate
• MS-26903
• CS-0018335
• Hastatoside1alpha-(beta-D-Glucopyranosyloxy)-1,4a,5,6,7,7aalpha-hexahydro-4aalpha-hydroxy-7alpha-methyl-5-oxocyclopenta[c]pyran-4-carboxylic acid methyl ester; Methyl (1S,4aR,7S,7aR)-4a-hydroxy-7-methyl-5-oxo-1-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy)-1H,4ah,5H,6H,7H,7ah-cyclopenta(C)pyran-4-carboxylate
• methyl (1S,4aR,7S,7aR)-4a-hydroxy-7-methyl-5-oxo-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-1,6,7,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6116	61.16%
Caco-2	-	0.8461	84.61%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7126	71.26%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8002	80.02%
OATP1B3 inhibitior	+	0.9444	94.44%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.7559	75.59%
P-glycoprotein inhibitior	-	0.8044	80.44%
P-glycoprotein substrate	-	0.7517	75.17%
CYP3A4 substrate	+	0.6239	62.39%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8877	88.77%
CYP3A4 inhibition	-	0.8928	89.28%
CYP2C9 inhibition	-	0.8927	89.27%
CYP2C19 inhibition	-	0.8971	89.71%
CYP2D6 inhibition	-	0.9299	92.99%
CYP1A2 inhibition	-	0.9155	91.55%
CYP2C8 inhibition	-	0.7263	72.63%
CYP inhibitory promiscuity	-	0.8395	83.95%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6363	63.63%
Eye corrosion	-	0.9878	98.78%
Eye irritation	-	0.9624	96.24%
Skin irritation	-	0.7349	73.49%
Skin corrosion	-	0.9450	94.50%
Ames mutagenesis	-	0.6154	61.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.6317	63.17%
Micronuclear	-	0.6000	60.00%
Hepatotoxicity	-	0.6699	66.99%
skin sensitisation	-	0.8682	86.82%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.5407	54.07%
Acute Oral Toxicity (c)	III	0.4534	45.34%
Estrogen receptor binding	-	0.5000	50.00%
Androgen receptor binding	+	0.5882	58.82%
Thyroid receptor binding	-	0.5406	54.06%
Glucocorticoid receptor binding	-	0.5686	56.86%
Aromatase binding	-	0.5497	54.97%
PPAR gamma	-	0.6157	61.57%
Honey bee toxicity	-	0.7977	79.77%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	+	0.7197	71.97%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.70%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.18%	96.09%
CHEMBL2581	P07339	Cathepsin D	93.10%	98.95%
CHEMBL4040	P28482	MAP kinase ERK2	91.70%	83.82%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.12%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.80%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.05%	97.09%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	83.23%	91.24%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.41%	94.00%
CHEMBL5255	O00206	Toll-like receptor 4	81.02%	92.50%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.00%	95.83%
CHEMBL3401	O75469	Pregnane X receptor	80.68%	94.73%
CHEMBL4208	P20618	Proteasome component C5	80.62%	90.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	80.28%	96.61%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.01%	99.23%

Plants that contains it

• Penstemon bradburyi
• Penstemon nitidus
• Penstemon secundiflorus
• Verbena hastata
• Verbena officinalis

Cross-Links

• PubChem: 92043450
• LOTUS: LTS0272417
• wikiData: Q72481072